반응 #319550

반응 방정식

2'-deoxy-5-ethyluridine

p-toluenesulfonyl chloride

→

2'-deoxy-5-ethyl-5'-O-(p-toluenesulfonyl)uridine

수율 31.2%

용매

pyridine

반응 조건

후처리

1. 1
   workup.ADDITIONwere added portionwise
2. 2
   workup.WAITthe mixture was then left
3. 3
   workup.WAITto stand at 4° C. overnight
4. 4
   기타The solvent was removed by evaporation
5. 5
   기타the residue was re-evaporated with toluene
6. 6
   workup.STIRRINGThe residue was shaken with 200 ml of methanol
7. 7
   workup.WAITleft
8. 8
   workup.WAITto stand in a refrigerator for 2.5 hours
9. 9
   기타to give a solid which
10. 10
    기타was removed by filtration
11. 11
    세척washed with methanol
12. 12
    기타dried in vacuo
13. 13
    기타to give 18 g of crude product of melting point 183° C. (decomposition)
14. 14
    기타Recrystallization from 450 ml of ethanol

실험 절차

26 g of 2'-deoxy-5-ethyluridine were dissolved in 400 ml of dry pyridine. The solution was cooled to 0° C. and stirred while 20 g of p-toluenesulfonyl chloride were added portionwise. Stirring at 0° C. was continued for 1 hour and the mixture was then left to stand at 4° C. overnight. The solvent was removed by evaporation and the residue was re-evaporated with toluene. The residue was shaken with 200 ml of methanol and left to stand in a refrigerator for 2.5 hours to give a solid which was removed by filtration, washed with methanol and dried in vacuo to give 18 g of crude product of melting point 183° C. (decomposition). Recrystallization from 450 ml of ethanol gave 13 g of pure 2'-deoxy-5-ethyl-5'-O-(p-toluenesulfonyl)uridine of melting point 189°-190° C. (decomposition).

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